We tend to think about risk by only asking one question: How likely is it?
That's a useful question. But it’s only half of the calculation!
A small chance of scraping your knee is very different from a small chance of dying.
👉 Risk has two parts… How likely is it? And what happens if it does?
You need both answers!
That’s the idea behind sketch #51, The Math of Risk, from my new book, Your Money.
📘 You can order a copy for yourself here or anywhere you love to buy books: buff.ly/gwaUxP6
📚 To order in bulk as gifts for clients, colleagues, or friends, use this link to get an additional 5% off U.S. bulk orders with the code: YOURMONEY5. → buff.ly/uchPThE
Your Money is 101 simple sketches designed to start better conversations about money. Keep it on your coffee table, dog-ear the pages that make you think, and share a sketch when a money conversation with someone you love gets stuck.
What is investing actually for?
You could beat the market and still miss every financial goal you have. You could also trail the market and still do everything that matters to you.
An index doesn’t know where you’re trying to go!
💪 Your money's job is to help you reach the destination you want.
For my Real Financial Advisor friends…
This sketch gives you a clean way to discuss a concentrated stock, cryptocurrency, private deal, or other exciting idea without judging the client. Put it on the table and ask them to name the game. That changes the conversation quickly!
You can license the sketch for client meetings, onboarding at your firm, presentations, newsletters, videos, email, or social media. As always, license my sketches at the Sketch Store here: buff.ly/FpHHkay
For client copies of my latest book, Your Money, use code YOURMONEY5 for an additional 5% off U.S. bulk orders. buff.ly/Fdso69E 💌 If you're outside the United States and would like to place a bulk order, send an email to [email protected] and the team can help!
Diversification requires the humility to own something you dislike because you can't know what the future will favor.
A good story can make hope sound like research!
A smart friend told you about it, you read an article, you think you can explain why it should go up…
But before you invest, ask yourself, “What do I actually know?”
The market doesn’t care what we hope will happen.
This sketch is from my latest book, Your Money. You can order a copy for yourself here or anywhere you love to buy books: buff.ly/j9m6POP
To order in bulk as gifts for clients, colleagues, or friends, use this link to get an additional 5% off U.S. bulk orders with the code: YOURMONEY5. buff.ly/AzNCmFh
Leave a copy on your coffee table, in your conference room, or in the hands of the people who trust you!
When an investment has been doing well, buying it feels sensible.
You have proof. You can see the results!
The problem is that all the proof is behind you.
Past performance is information. It isn’t a plan.
We buy high and sell low, even though we know better.
At the top of the market, we can’t buy fast enough. At the bottom, we can’t sell fast enough.
Repeat until broke.
This behavior is normal, but acting on it can cost a lot!
My latest book, Your Money, was written for everyone brave enough to break the silence around money.
📚 If you’d like copies for your team, clients, or for the attendees of your next event, you can place U.S. orders in bulk at a discounted rate here: buff.ly/L8ORbhz
Use the code YOURMONEY5 for an extra 5% off.
Outside the U.S.? Email [email protected], and the team can help with a bulk order.
There’s a difference between what an investment earns and what an investor actually gets.
The return can happen. And we can still miss it.
Usually because we weren’t there long enough to receive it!
That’s what I like to call The Behavior Gap.
Clients often ask, “Should I spend less?”
Sometimes the better question is: “Is this way of spending actually giving you what you want?”
That question changes the conversation.
This idea comes from my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.
Want a copy?
📘 Order a copy for yourself on Amazon or your favorite bookstore buff.ly/kHLquwo
📚 Order in bulk to hand out to clients, prospects, or friends. Use this link to order and get an additional 5% off bulk orders (U.S. shipping only) with the code: ADVISOR5. buff.ly/BjBaO2g
🌎 If you're outside of the United States and would like to place a bulk order of 25+ copies, email the team at [email protected].
Leave a copy on your coffee table, in your conference room, or in the hands of the people who trust you!
Put this sketch in front of a client who feels guilty about spending and ask, “Does this line up with what matters most?”
When you tell yourself, “Don’t look, don’t look, don’t look,” but you still look.
Sometimes the move is to redirect.
When it comes to experiences with people you love, spend the money.
Not every time.
Not without thinking.
But more often than your spreadsheet might suggest.
📚 This sketch is from my latest book, Your Money: Reimagining Wealth in 101 Simple Sketches. Order your copy here: buff.ly/t9S8B0B
Cheap things can cost us money.
They can also cost us time, attention, and hassle.
That part matters, too.
→ This sketch comes from my latest book, Your Money: Reimagining Wealth in 101 Simple Sketches. You can order it wherever you buy books, or here:
buff.ly/GjHJgyx
At some point, the research costs more than the thing.
Just pick one and move on.
From my new book, Your Money: Reimagining Wealth in 101 Simple Sketches: buff.ly/GjHJgyx
Most financial goals sound exciting in the beginning.
💪 Retire early.
🌎 Travel more.
💰 Give more away.
But for Real Financial Advisors, almost every meaningful financial goal eventually runs into the same question:
👉 How’s the cash flow?
That’s not just math. That’s behavior!
It's where values become visible, where the real work lives.
These are the kinds of conversations I love having with advisory firms, leadership teams, and conference audiences. If you’d like me to speak at your next event, my team would love to help make it happen. 💌 Email [email protected] and let's talk.
Most people think saving money starts with restriction.
Sometimes it just starts with noticing.
One small positive outcome changes what feels possible. That’s why tiny wins matter so much with money.
We tend to think big goals require big action.
But most of the time, progress starts with one small move.
Saving for college feels overwhelming. Finding an extra $100 does not.
That’s the power of a micro-action. 💪 It creates momentum, and momentum has a way of spreading.
Start there. Then see what happens next.
This sketch is from my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.
If you’d like copies for your team, clients, or for the attendees of your next event, U.S. orders have a discounted bulk rate here: buff.ly/Wrqn78Q. Use the code YOURMONEY5 for an additional 5% off.




















